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A kind of andrographolide-19-o-glucoside and its preparation method and application in the preparation of anti-inflammatory drugs

A technology of andrographolide and glucoside, which is applied in the direction of anti-inflammatory agents, drug combinations, antipyretics, etc., can solve the problems of poor stereo and regioselectivity, residual chemical substances, easy to produce by-products, etc., and achieve stereo and regioselectivity The effect of good sex, high purity and good medicinal prospect

Inactive Publication Date: 2020-09-04
JINAN UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method synthesizes andrographolide-19-O-glucoside, which has large energy consumption, poor stereo and regioselectivity, and easily produces by-products; and due to the use of a large amount of toxic organic solvents and catalysts in the reaction process, it will cause serious Environmental pollution problems, on the other hand, there are often some toxic chemical substances left in the product, which poses a safety hazard
The other is the preparation of andrographolide-19-O-glucoside by biosynthesis (Ying Qiao; Yao Huang; Fang Feng; Zhi-Gang Chen; Efficient enzymatic synthesis and antibacterial activity of andrographolide glycoside; Process Biochemistry 51(2016) 675–680 ), this method has reported the synthesis of andrographolide-19-O-galactoside in the current literature, and the yield is relatively low (about 25.5~67.5%)

Method used

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  • A kind of andrographolide-19-o-glucoside and its preparation method and application in the preparation of anti-inflammatory drugs
  • A kind of andrographolide-19-o-glucoside and its preparation method and application in the preparation of anti-inflammatory drugs
  • A kind of andrographolide-19-o-glucoside and its preparation method and application in the preparation of anti-inflammatory drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042]1.75g ​​of andrographolide, 25mM of uridine-5'-diphosphate glucose sodium salt (UDPG), 2g of ASP (A242V / S132F / P67T) glycosyltransferase ( The preparation method refers to the literature Williams, Gavin J; Zhang, Changsheng; Thorson, Jon S; Expanding the promiscuity of a natural-product glycosyltransferase by directed evolution; Nat Chem Biol, 2007, 3, 657-662) and 5mM MgCl 2 , 50mM Tris-HCl (pH 8.0) mixed, placed in an incubator at 37°C, reacted for 16h, centrifuged at 12000rpm for 15min, concentrated the supernatant, put the mixture on a macroporous resin column, and eluted with pure water for 2 retention volumes , remove water-soluble impurities, then use 50% ethanol to elute 2 retention volumes, after 50% ethanol eluate is concentrated, promptly obtain andrographolide-19-O-glucoside (productivity 80%), biosynthesis roadmap see figure 1 .

[0043] The characterization diagram of the obtained product is shown in Figure 2 to Figure 5 , according to the high-resolutio...

Embodiment 2

[0047] 1.75g ​​of andrographolide, 50mM uridine-5'-diphosphoglucose sodium salt (UDPG), 2g of ASP(A242V / S132F / P67T) glycosyltransferase expressed in Escherichia coli BL21(DE3)PLysS and 5mM MgCl 2 , 50mM Tris-HCl (pH 8.0) mixed, placed in an incubator at 37°C, reacted for 16h, centrifuged at 12000rpm for 15min, concentrated the supernatant, put the mixture on a macroporous resin column, and eluted with pure water for 2 retention volumes , remove water-soluble impurities, and then use 50% ethanol to elute 2 retention volumes, and after the 50% ethanol eluate is concentrated, andrographolide-19-O-glucoside (yield 99%) is obtained.

Embodiment 3

[0049] 1.75g ​​of andrographolide, 25mM of uridine-5'-diphosphate glucose sodium salt (UDPG), 2g of ASP (A242V / S132F / P67T) glycosyltransferase derived from the expression of Escherichia coli BL21 (DE3) PlysS and 5mM MgCl 2 , 50mM Tris-HCl (pH 6.0) mixed, placed in an incubator at 37°C, reacted for 16h, centrifuged at 12000rpm for 15min, concentrated the supernatant, put the mixture on a macroporous resin column, and eluted two retained volume, remove water-soluble impurities, then use 50% ethanol to elute 2 retention volumes, after 50% ethanol eluate is concentrated, obtain white powder, be andrographolide-19-O-glucose (productivity 37% ).

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Abstract

The invention belongs to the technical field of biological synthesis of biocatalyst, and discloses andrographolide-19-O-glucoside and a preparation method thereof, as well as application in preparation of an anti-inflammatory drug. The method specifically comprises the following steps: taking uridine-5'-glucose disodium diphosphate as a glycosyl donor in a buffer solution system, and catalyzing andrographolide by applying a mutant A242V / S132F / P67T of glycosyl transferase OleD for glycosylation reaction, thus obtaining the andrographolide-19-O-glucoside. The andrographolide-19-O-glucoside obtained through the method can be applied to preparation of the anti-inflammatory drug; via glycosylation treatment, the andrographolide-19-O-glucoside greatly increases the water solubility of the drug and improves the original anti-inflammatory activity of the drug. According to the preparation method, the glycosyl transferase is adopted to perform glycosylation modification on the andrographolide for the first time; the reaction system has the advantages of mild reaction condition, low energy consumption, high yield, stereoscopic impression, high region selectivity, small quantity of byproducts, easiness for separation of a product and the like.

Description

technical field [0001] The invention belongs to the technical field of biocatalyst biosynthesis, and particularly relates to an andrographolide-19-O-glucoside, a preparation method thereof and an application in preparation of anti-inflammatory drugs. Background technique [0002] Andrographolide (andrographolide) is a diterpene lactone compound in the Acanthaceae plant Andrographis paniculata, and it is one of the main active ingredients of the traditional Chinese medicine Andrographis paniculata (N.Pholphana; N.Rangkadilok; S.Thongnest; S.Ruchirawat; M.Ruchirawat ; J. Satayavivad; Determination and variation of threeactive diterpenoids in Andrographis paniculata (Burm. f.) Nees, Phytochem. Anal. 15 (2004) 365–371.). Andrographolide mainly exists in leaves (about 0.5-1.0%), and has good antibacterial, anti-inflammatory, antiviral and other functions. Since the maximum solubility of andrographolide in water is only 60 μg / mL, and it is insoluble in most organic solvents, its ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P19/46A61K31/7048A61P29/00
CPCA61K31/7048C12P19/46
Inventor 江仁望朱雪林文超
Owner JINAN UNIVERSITY
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